WO2020007775A1

WO2020007775A1 - Active substances for high-viscosity washing and cleaning formulations

Info

Publication number: WO2020007775A1
Application number: PCT/EP2019/067540
Authority: WO
Inventors: Stefan Neubauer; Jens Hildebrand; Dirk Kuppert
Original assignee: Evonik Operations Gmbh
Priority date: 2018-07-05
Filing date: 2019-07-01
Publication date: 2020-01-09
Also published as: EP3818137B1; CN112368362A; US20210277329A1; US11692153B2; BR112020026982A2; EP3818137A1; CN112368362B; ES2936215T3

Abstract

The invention relates to special active substances for producing highly viscous washing and cleaning agents, in particular fabric softener, and to a method for the production thereof, and to said washing and cleaning formulations. The high viscosity can be achieved in the claimed products despite a low concentration of active substances and without using additional thickeners.

Description

Active ingredients for highly viscous washing and cleaning formulations

The invention relates to special active ingredients for the production of highly viscous washing and

Cleaning formulations, in particular fabric softeners, a process for their preparation and washing and cleaning formulations containing said active ingredients. The high viscosity of the products according to the invention can be achieved despite the low concentration of active substances and without the use of additional thickeners.

1. State of the art

In regional markets such as Brazil, washing and cleaning formulations, in particular fabric softeners, are in demand, which have low active contents, i.e. low content of quaternary ammonium compounds, high viscosity.

Simply by using quaternary ammonium compounds, hereinafter also referred to as "quats" or "esterquats", such as Rewoquat WE 18, the required viscosity has not been achieved so far. With triethanolamine-based ester quats, as described, for example, in WO 2014/143182 A2, DE 10 2010 030 217 A1 and DE 197 43 687 C1, only viscosities of at most 500 mPas could be achieved when the quat was used alone.

DE2928603 discloses so-called “hybrid” quats, among other things. These are characterized in that, in addition to alkanol and alkanol ester residues, they also have a long-chain alkyl residue. The hybrid quats of DE2928603 are said to give the laundry a pleasant soft feel. Viscosities of the fabric softener produced with these hybrid quats are not specified in DE 2928603. However, there is an indication that the viscosity of other substances and auxiliaries must be added to the fabric softener. Such addition of auxiliaries, in particular thickeners, is common in the prior art, but has ecological and economic disadvantages.

WO 2016/055341 describes active substances comprising bis (2-hydroxypropyl) dimethylammonium methyl sulfate fatty acid esters with which aqueous and storage-stable

Fabric softener formulations with high viscosity can be produced. A disadvantage of these active substances is that relatively large amounts have to be used to increase the viscosity.

US 2006/0264352 A1 describes fabric softener formulations containing esterquat with a high viscosity. To achieve the high viscosity, long-chain alkyl amines must be added as viscosity regulators.

There is therefore a need for new active substances and for washing and cleaning formulations, especially fabric softeners that do not have the disadvantages of the prior art or only have them to a reduced extent, preferably that can make the use of thickeners obsolete.

2nd task

The object of the present invention was therefore to provide new active substances and new washing and cleaning formulations, in particular fabric softener formulations, which do not have the disadvantages of the prior art or only have them to a reduced extent.

In a special task, the washing and cleaning formulations, without the addition of additional thickeners, should have a sufficiently high viscosity at the low active content required solely through the active substances according to the invention.

In a further object, it should be possible to adjust the viscosity of washing and cleaning formulations in a very wide range solely by using the active substances according to the invention. In a further preferred object, the fabric softener products according to the invention are intended to have an at least comparable fabric softening effect to products of the prior art.

Another object can be seen in providing washing and cleaning formulations, in particular fabric softener products, which are biodegradable.

Further tasks that are not explicitly mentioned result from the overall context of the present description, claims and examples.

3. Definitions

Before the invention is described in detail, a few terms are first defined:

In the context of the present invention, “active substances” are understood to mean compositions comprising mixtures of esterquats of the general formula I defined in more detail below. The activity of these esterquats is demonstrated, among other things, by their thickening effect, but also by their fabric softening effect. The active substances can consist exclusively of esterquats of the general formula I, but they can also, for example for better handling, be diluted with a solvent. "Washing and cleaning formulations" includes all types of washing and

Cleaning formulations understood in which esterquats are commonly used. These are preferably fabric softener formulations. The washing and cleaning formulations according to the invention can contain the active substances according to the invention, but can also consist only of them. In addition to the active substances according to the invention, they usually also contain at least one perfume oil and water.

In the context of the present invention, “high viscosity” means a viscosity of more than 500 mPas, preferably more than 750 mPas, particularly preferably more than 1000 mPas.

In the context of the present invention, washing and cleaning formulation with “low active content” is understood to mean a washing and cleaning formulation which has a total active ingredient content of less than 5% by weight, particularly preferably less than 3% by weight, based on the overall composition of the washing and

Have cleaning formulations.

4. Detailed description of the invention

Surprisingly, it was found that active substances according to claim 1 and washing and

Cleaning formulations, in particular fabric softener formulations, containing these active substances, according to claim 7, solve the stated problems. The active substances according to the invention contain mixtures of special ester quats of the general formula I defined in more detail below. Their use has resulted in fabric softener formulations which, despite their low active substance content, have a high viscosity. The viscosities were at least 10% above the maximum 500 mPas achieved in the prior art and ranged up to 2400 mPas. It was thus made possible solely by using the active substances according to the invention, the viscosity of the

Adjust fabric softener formulation in a very wide range with a low active ingredient content.

The esterquats used according to the invention enable the production of ecologically advantageous washing and cleaning formulations.

The washing and cleaning formulations according to the invention can also be prepared without the addition of thickeners with a high viscosity and a low content of active substances. This increases the ecological, but also brings economic advantages. However, the fact that the washing and cleaning formulations according to the invention can be produced without the addition of thickeners does not fundamentally preclude their use.

The present invention thus relates to active substances as claimed in claim 1 and to a process for their preparation as claimed in claim 6 Cleaning formulation, preferably fabric softener formulation, containing the active substances according to the invention as claimed in claim 7 and the use of

Active substances according to the invention as claimed in claim 8. Preferred embodiments are claimed in the subclaims.

The present invention relates in particular to active substances for the preparation of washing and cleaning formulations, preferably fabric softener formulations, which are characterized in that they are a mixture of several quaternary ammonium salts of the general formula I)

R ¹

R ³ - O - R ² - N ⁺ - R ⁴ - O - R ⁵ xr

R ⁶ general formula I) with

R ^{1 is} a linear or branched hydrocarbon radical with an iodine number less than or equal to 10, preferably less than or equal to 8, particularly preferably from 0 to 5, having 10 to 32 carbon atoms, preferably 12 to 22 carbon atoms, particularly preferably 14 to 20 carbon atoms and in particular 16 to 18 carbon atoms .

R ² , R ^4, independently of one another, identical or different, selected from the group of double-bonded, preferably linear, hydrocarbon radicals having 1 to 4

Carbon atoms, preferably methylene, ethylene, and n-propylene, particularly preferably ethylene,

R ^{3 is} hydrogen or an acyl residue of a fatty acid with a chain length of 8 to 32

Carbon atoms, preferably 12 to 22 carbon atoms, in particular 14 to 18 carbon atoms,

R ^5, identical or different from R ³ , hydrogen or acyl radical of a fatty acid with a chain length of 8 to 32 carbon atoms, preferably 12 to 22 carbon atoms, in particular 14 to 18 carbon atoms,

R ⁶ hydrocarbon radical having 1 to 4 carbon atoms, preferably methyl or ethyl, particularly preferably methyl,

X methyl sulfate or ethyl sulfate,

contain, the ratio of the quaternary ammonium salts of the general

Formula I) in the mixture results in that one or more amine (s) of the general formula

general formula II), where R ¹ , R ² and R ^{4 have} the same meaning as in formula I, with one or more fatty acids corresponding to R ³ and R ⁵ , in a molar ratio of the sum of all the amines of the general formula II) to the sum of all the fatty acids of 0.8 to 1.5, preferably 0.8 to 1.4, particularly preferably 0.85 to 1.3, and very particularly preferably 0.9 to 1.2.

As shown in Comparative Example V7, too low a molar ratio does not lead to

Active substances according to the invention with significantly lower thickening ability. An excessively high molar ratio leads to the same effect, i.e. to a decrease in thickening ability.

The choice of quaternization alkylating agent, especially X, also has a significant impact on the quat's ability to thicken. As in the

Comparative examples V1 and V2 shown quats with X = CI thicken much worse than those with X = MeSO

Finally, the inventors surprisingly found that the alkyl radical R ¹ should have a high mobility, ie a small number of double bonds, preferably no double bonds. This is demonstrated in the examples when comparing R ¹ = tallow (see

Comparative examples V3 to V6) with R ¹ = hydrogenated tallow shown. The proportion of double bonds in R ¹ is expressed by the iodine number. The radicals R ^{1 used} according to the invention have an iodine number of less than or equal to 10, preferably less than or equal to 8, particularly preferably from 0 to 5.

R ¹ is preferably a hydrocarbon radical which represents the hydrocarbon radical of fatty alcohols. A "hydrocarbon residue of fatty alcohol" in connection with the present earth invention is the remaining structure after deletion of the OH group of the fatty alcohol. A preferred radical R ¹ is a hydrocarbon radical of an unbranched or branched monoalcohol with an alkyl group of 10 to 22 carbon atoms. Preferred radicals R ¹ are

Hydrocarbon residues of cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, anteisostearyl alcohol, eicosanol, petroselinyl alcohol, Guerbet alcohol, arachyl alcohol,

Gadoleyl alcohol, and mixtures thereof, in particular technical mixtures, preferably technical stearyl, palmityl or hydrogenated tallow fatty alcohols having 12 to 22, preferably 14 to 20 carbon atoms, and monounsaturated fatty alcohols such as oleyl alcohol, elaidyl alcohol, delta-9 cis-hexadecenol, delta-9-octadecenol, trans-delta-9-octadecenol, cis-delta-1 1-octadecenol, trans-10, cis-12-hexadecadien-1-ol, octacosa-10, 19-dien-1 -ol wherein hydrocarbon residues from mixtures of stearyl or hydrogenated tallow fatty alcohols with 14 to 22, particularly preferably 14 to 18 and very particularly preferably 16 to 18

Carbon atoms are particularly preferred.

If mixtures of hydrocarbons of fatty alcohols, in particular technical mixtures, are used as R ¹ , the iodine number is the average iodine number of the mixture. The same applies to the fatty acids described below, ie the radicals R ³ and R ⁵ . Since the quats of the general formula I are obtained by reacting one or more amine (s) of the general formula II) defined above with one or more fatty acids corresponding to R ³ and R ⁵ , in the molar ratio defined above, it follows that some of the OH groups of the amine are retained as such. This is important to ensure the correct polarity of the quats. It also follows that the reaction gives a mixture of different quats of the general formula I in which either both OH groups or only one OH group or no OH group is esterified. Thus, R ³ and R ⁵ can either be both acyl or both H or one of both acyl and one H. If the radicals R ³ and R ^{5 are} both acyl radicals, they are preferably acyl esters of the same fatty acid or

Fatty acid remainder.

Preferred fatty acids for R ³ and R ⁵ are selected from

Vegetable or tallow fatty acids, preferably with an iodine number of 0 to 50, particularly preferably 5 to 45, very particularly preferably 10 to 25,

Vegetable or tallow fatty acids with an iodine number less than or equal to 10, preferably less than or equal to 8, particularly preferably from 0 to 5,

the fatty acids corresponding to the alkyl radicals R ¹ defined above as preferred

R ² and R ⁴ are preferably identical and preferably both equal C2H4 or both equal C3H6, particularly preferably both equal C2H4.

Particularly preferred active substances according to the invention are mixtures quaternary

Ammonium compounds of the general formula I), where the radicals R ¹ to R ⁶ and X are selected from the following groups:

R ^{1 is} a linear alkyl radical having 14 to 20, preferably 16 to 18 carbon atoms with an iodine number less than 8, preferably less than or equal to 5,

R ² , R ^{4 are} equal to C2H4,

R ³ , R ^5, independently of one another, identical or different, identical to hydrogen or an acyl radical of a fatty acid with a chain length of 12 to 22 carbon atoms, preferably 16 to 18 carbon atoms,

R ^{6 is} methyl or ethyl, preferably methyl,

X methyl sulfate or ethyl sulfate, preferably methyl sulfate

The active substances according to the invention result in the washing and cleaning formulations thus produced, preferably fabric softener formulations, having high viscosities even at low contents of these active substances and without additional thickeners. The washing and cleaning formulations according to the invention are preferred Fabric softener formulations thus contain the active substances according to the invention preferably in an amount of 1% by weight to 6% by weight, particularly preferably 2% by weight to 5% by weight, the weight percent based on the total composition. In addition, the washing and cleaning formulations can be preferred

Fabric softener formulations, water and other additive and / or auxiliary, e.g. selected from the group of emollients, pearlescent additives, dyes, insect repellents,

Preservatives, perfumes, dyes and defoamers in the washing and

Cleaning formulations may be included. The amounts of the respective additives depend on the intended use.

Typical frame formulations for the respective applications are known in the art and are contained, for example, in the brochures of the manufacturers of the respective base and active ingredients. These existing formulations can usually be adopted unchanged. If necessary, the desired modifications can be made without complications by simple experiments for adaptation and optimization

The active substances according to the invention are preferably produced by a process which comprises the following steps:

a) reaction of one or more amine (s) of the general formula (II),

General formula (II), where R ¹ , R ² and R ^{4 have} the same meaning as above, with one or more fatty acid (s) with a chain length of 8 to 32 carbon atoms, preferably 12 to 22 carbon atoms, particularly preferably 16 to 18 Carbon atoms, in a molar ratio of the sum of all amines of the general formula (II) to the sum of all fatty acids from 0.8 to 1.6, preferably 0.8 to 1.5, particularly preferably 0.8 to 1.5, very particularly preferably 0 , 8 to 1, 4, particularly preferably 0.85 to 1, 3, and very particularly preferably 0.9 to 1, 2 are implemented

b) reaction of the amines from step a) with an alkylating agent selected from the group consisting of dimethyl sulfate and diethyl sulfate, for the preparation of quaternary ammonium salts of the formula (I). The active substance mixture obtained after step b) is preferably used for better handling in step

c) with 30-40% by weight, preferably 10-20% by weight, of a water-miscible solvent

diluted. Such solvents are, for example, ethanol, 1-propanol, 2-propanol, 1, 2- Ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol, dipropylene glycol, ethylene glycol ether or propylene glycol ether or mixtures thereof.

The active substances according to the invention particularly preferably consist only of the mixture contained after step b) or of the dilute mixture obtained after step c).

Technologies for carrying out steps a) and b) are known per se to the person skilled in the art.

The active substances according to the invention obtained after step b) or c) are preferred for the preparation of the washing and cleaning formulations according to the invention

Fabric softener formulations, preferably processed as follows:

Water is placed in a stirred tank and heated to a temperature between 20 and 60 ° C. The active ingredients are melted and brought to a temperature between 30 and 60 ° C. The melt is introduced into the water reservoir with thorough stirring. The dispersion thus obtained is cooled and optionally further additives, described in more detail below, are added.

As already mentioned, the active substances according to the invention are used as active substances in washing and cleaning formulations. You can do this in principle in any washing and

Cleaning formulations are used in the usual way Quats are used.

They are particularly preferably used in washing and cleaning formulations which have a high viscosity and very particularly preferably in those which are said to have a high viscosity with a low active content.

The washing and cleaning formulations are most preferably

Softener. Preferred fabric softener formulations according to the invention for household, industrial and institutional applications, containing at least one of the active substances according to the invention, are detergents, laundry care products, disinfectant laundry detergents, heavy duty laundry detergents, mild detergents, wool laundry detergents, fabric softeners and impregnating agents, detergents, laundry care agents, heavy duty detergents, mild detergents, wool detergents, fabric softeners, fabric softeners

especially fabric softeners are particularly preferred.

A fabric softener formulation according to the invention preferably contains the active substances according to the invention in an amount of 1% by weight to 5% by weight, preferably 2% by weight to 4% by weight, the% by weight based on the total formulation. The remaining 100% by weight preferably consists of water and / or at least one additive and / or auxiliary, selected from the group of emollients, viscosity regulators, pearlescent additives, dyes,

Insect repellents, preservatives, perfumes, dyes and defoamers. All perfumes or fragrance mixtures known to be suitable for fabric softeners from the prior art can be used as the perfume, preferably in the form of a perfume oil. Examples of fragrance or fragrance substances are disclosed, inter alia, in DE 197 51 151 A1, page 4, line 1 1-17. In particular, the compositions according to the invention can contain from 0.01 to 10% by weight, particularly preferably 0.1 to 5% by weight, based on the overall composition of the composition of one or more perfumes.

All dyes known to be suitable for fabric softeners from the prior art can be used as dyes, water-soluble dyes being preferred. Examples of suitable water-soluble commercial dyes are SANDOLAN ^® Walkblau NBL 150 (manufacturer Clariant) and Sicovit ^® Azorubin 85 E122 (manufacturer BASF). In particular, the compositions according to the invention can contain from 0.001 to 0.1% by weight, particularly preferably from 0.002 to 0.05% by weight, of one or more dyes.

As already mentioned above, the washing and

Cleaning formulations, in particular fabric softener formulations, no viscosity regulators are required, since the viscosity can be adjusted using only the active substances according to the invention. However, it is not excluded to add other viscosity regulators. So as a viscosity regulator to reduce the viscosity alkali metal or

Alkaline earth metal salt, or mixtures thereof, preferably calcium chloride, preferably in an amount of 0.05 to 2% by weight, based on the total composition of the composition.

As a viscosity regulator to increase the viscosity, the fabric softener can contain a thickener known from the prior art, the thickeners known from WO 2007/125005

Polyurethane thickeners are preferred. Examples of suitable thickeners are TEGO ^® Visco Plus 3030 (manufacturer Evonik Tego Chemie), Acusol ^® 880 and 882 (manufacturer Rohm & Haas),

Rheovis ^® CDE (manufacturer BASF), Rohagit ^® KF 720 F (manufacturer Evonik Rohm GmbH) and Polygel ^® K100 from Neochem GmbH.

Any defoamers known to be suitable for fabric softeners from the prior art can be used as defoamers. Examples of suitable commercially available defoamers are Dow Corning ^® DB-1 10A and TEGO ^® Antifoam ^® 7001 XP. In particular, the compositions according to the invention can contain from 0.0001 to 0.05% by weight, preferably from 0.001 to 0.01% by weight, of one or more different defoamers.

As a preservative, the fabric softener from the prior art can contain known bactericidal and / or fungicidal active substances, water-soluble active substances being preferred. Examples of suitable commercial bactericides are methylparaben, 2-bromo-2-nitro-1,3-propanediol, 2-methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4-isothiazolin-3-one. Likewise, the aqueous fabric softener contain an oxidation inhibitor as a preservative. Examples of suitable commercially available oxidation inhibitors are ascorbic acid, 2,6-di-tert-butyl-4-methylphenol (BHT), butylated hydroxyanisole (BHA), tocopherol and propyl gallate. In particular, the compositions according to the invention can contain from 0.0001 to 0.5, particularly preferably 0.001 to 0.2% by weight of one or more different preservatives. In particular, the compositions according to the invention can contain from 0.001 to 0.1% by weight, preferably 0.001 to 0.01% by weight, of one or more different oxidation inhibitors.

The amounts of the respective additives depend on the intended use.

Typical frame formulations for the respective applications are known in the art and are contained, for example, in the brochures of the manufacturers of the respective base and active ingredients. These existing formulations can usually be adopted unchanged. If necessary, the desired modifications can be made without complications by simple experiments for adaptation and optimization.

5. Measurement methods

5.1 Determination of the iodine number

The iodine number indicates how many grams of halogen, calculated as iodine, from 100 g of an examined sample are bound under the conditions of a method. The measurement method according to Wijs according to DIN 53241-1: 1995-05 is used according to the invention.

While the iodine number of the radical R ¹ on the amine of the general formula (II) can be measured directly, the iodine number of the quaternary ammonium compound of the general formula (I) is measured by first saponifying acyl residues under alkaline conditions and the fatty acid and ammonium compound thus obtained according to known methods Separates methods. The iodine number of R ¹ , from which

Ammonium compound, and that of the fatty acid can then be determined using the Wijs method.

5.2 Determination of the viscosity of the washing and cleaning formulations

The viscosity is measured using a Brookfield LVT viscometer and a spindle suitable for the viscosity range at a temperature of 25 ° C and 30 rpm. 6. Examples

In the examples listed below, the present invention is described by way of example, without the invention, the breadth of its application being from the whole

Description and claims, to which the embodiments mentioned in the examples should be limited.

6.1 Starting materials used: 6.1.1 Amines of the general formula II:

Table 1 :

6.1.2 Fatty acids:

Table 2:

6.1.3 Alkylating agents Table 3:

6.2 General manufacturing instructions for quaternary ammonium compounds: Example B1:

571, g (1, 588 mol) of amine A1 were placed in a three-necked flask with column, distillation bridge and stirrer motor and heated to 80 ° C. under a nitrogen atmosphere. 352.2 g (1, 271 mol) of fatty acid FS 3 and 0.46 g of 50% aqueous hypophosphorous acid were added. A vacuum of 100 mbar was applied and carefully warmed to 195 ° C., where

Reaction water was caught in the outlet of the distillation bridge. After 2.5 hours, the vacuum was reduced to 20 mbar and the reaction continued for 1.5 hours. The condensation product thus obtained had an acid number of 0.9 mg KOH / g and an amine number of 96.2 mg KOH / g. The reaction mixture was cooled to 80 ° C. 186.2 g (1, 477 mol) of dimethyl sulfate were added dropwise with stirring in the course of one hour, the temperature being kept in a range from 80 ° -95 ° C. Then 120 g of anhydrous ethanol were added and the mixture was stirred at 80 ° C. for one hour. The quat mixture thus obtained had an amine number of 3.1 mg KOH / g.

The other examples and comparative examples were carried out in accordance with this specification, however, with varied starting materials or varying proportions - in each case as indicated in Tables 4 and 5 below. 6.3 Application tests

Table 4 shows various washing and cleaning formulations according to the invention as examples. In each case, according to the instructions under 6.2, according to the information in Table 4, Quat mixtures were prepared and mixed with water, so that each formulation of 3% by weight Quat mixture (calculated on the solids content), 0.2% Perfume oil, and water ad 100% resulted. The viscosity was determined in each case from the formulation obtained.

Table 4:

For comparison, examples not according to the invention are shown in Table 5, in which:

In V1 and V2 MeCI instead of DMS as alkylating agent

In V3 to V6 the amine A2 substituted with R ^{1 on the} same day with an iodine number of 18-22 instead of the tallow equally hydrogenated with R ¹ with an iodine number of <1.0

A3

In V7 an amine with a molar ratio less than 0.8

was used. Table 5:

The comparisons of V1 with B2 and of V2 with B6 show that the use of DMS instead of MeCI as an alkylating agent contributes significantly to achieving the object of the present invention.

The comparisons of V3 with B7, V4 with B6, V5 with B7 and V6 with B2 show that the use of residues R ¹ with an iodine number less than 10 instead of a residue R ¹ with a high iodine number under otherwise identical conditions leads to significantly higher viscosities leads. The comparison of V7 with B1 to B3 shows the influence of the molar ratio of fatty acid to amine. If this is too low, as in V7, a sufficient thickening effect is not achieved.

Claims

Expectations

1. Active ingredient for the production of washing and cleaning formulation, preferred

Fabric softener formulation containing

a mixture of several quaternary ammonium salts of the general formula I)

general formula I) with

R ² , R ⁴ independently of one another, identical or different, selected from the

Group of divalent, preferably linear, hydrocarbon radicals having 1 to 4 carbon atoms, preferably methylene, ethylene, and n-propylene, particularly preferably ethylene,

Carbon atoms, preferably 12 to 22 carbon atoms, in particular 16 to 18 carbon atoms,

R ^{5 is} identical or different from R ³ , hydrogen or acyl radical of a fatty acid with a chain length of 8 to 32 carbon atoms, preferably 12 to 22

Carbon atoms, in particular 16 to 18 carbon atoms,

X methyl sulfate or ethyl sulfate,

in which

the quantitative ratio of the quaternary ammonium salts of the general formula I) in the mixture results from the fact that one or more amine (s) of the general formula II)

general formula II), where R ¹ , R ² and R ^{4 have} the same meaning as in formula I), with one or more fatty acids corresponding to R ³ and R ⁵ , in a molar ratio of the sum of all amines of the general formula II) to the sum all fatty acids from 0.8 to 1.5, preferably 0.8 to 1.4, particularly preferably 0.85 to 1.3, and very particularly preferably 0.9 to 1.2, are reacted.

2. active substance according to claim 1,

characterized,

that one or both of R ² and R ^{4 are} equal to ethylene.

3. active substance according to claim 1 or 2,

characterized,

that in the radicals R ³ and R ^5, provided that they are acyl radicals, acyl radicals of the same

Are fatty acid or fatty acid mixture.

4. active substance according to one of claims 1 to 3,

characterized,

that the mixture contains quaternary ammonium compounds of the general formula I) with

R ² , R ^{4 are} equal to C ₂ H ₄ ,

R ³ , R ^5, independently of one another, identical or different, hydrogen or acyl radical of a fatty acid with a chain length of 12 to 22 carbon atoms, preferably 16 to 18 carbon atoms,

R ^{6 is} methyl or ethyl, preferably methyl,

X methyl sulfate or ethyl sulfate.

5. active substance according to claims 1 to 4,

characterized,

that R ³ and R ⁵ , if it is an acyl radical, are selected from acyl radicals of

- Vegetable or tallow fatty acids, preferably with an iodine number of 0 to 50, particularly preferably 5 to 4, and very particularly preferably 10 to 25

Vegetable or tallow fatty acids with an iodine number of less than or equal to 10, preferably less than or equal to 8, particularly preferably from 0 to 5,

6. A process for the preparation of an active substance, according to one of claims 1 to 5,

characterized in that it comprises the following steps

a) reaction of one or more amine (s) of the general formula II),

general formula II), where R ¹ , R ² and R ^{4 have} the same meaning as in claim 1, with one or more fatty acid (s) with a chain length of 8 to 32 carbon atoms, preferably 12 to 22 carbon atoms, particularly preferably 16 to 18 carbon atoms, in a molar ratio of the sum of all amines of the general formula II) to the sum of all fatty acids from 0.8 to 1.6, preferably 0.8 to 1.5, particularly preferably 0.8 to 1.5, very particularly preferably 0 , 8 to 1, 4, particularly preferably 0.85 to 1, 3, and very particularly preferably 0.9 to 1, 2,

b) reaction of the amines from step a) with an alkylating agent, selected from the group consisting of dimethyl sulfate, for the production of quaternary

Ammonium salts of formula I)

as well as optional

c) diluting the active substance mixture obtained after step b) with 30-40% by weight, preferably 10-20% by weight, of a water-miscible solvent, preferably with one or more solvents selected from the group consisting of ethanol, 1-propanol, 2-propanol, 1, 2-ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol, dipropylene glycol, dipropylene glycol, ethylene glycol ether or propylene glycol ether.

7. washing and cleaning formulation, preferably fabric softener formulation, containing an active substance, according to one of claims 1 to 5.

8. washing and cleaning formulation, preferably fabric softener formulation, according to claim 7, characterized in that it contains the active substance in an amount of 1% by weight to 6% by weight, preferably 2% by weight to 5% by weight, the percentages by weight on the

Get total composition, contains.

9. washing and cleaning formulation, preferably fabric softener formulation, according to claim 7 or 8, characterized in that it has a viscosity of more than 500 mPas, preferably more than 750 mPas, particularly preferably more than 1000 mPas, measured with a

Brookfield viscometer LVT and a spindle suitable for the viscosity range at a temperature of 25 ° C and 30 U / min.

10. Use of at least one active substance according to one of claims 1 to 5 as or in

Washing and cleaning formulations, especially as fabric softener or in

Softeners.